Because of the lack of effective alkylating reagents, alkyl etherification of olefins with general alkyl groups has not been previously reported. In this work, a variety of alkyl diacyl peroxides and peresters generated from aliphatic acids have been found to enable the first iron-catalyzed alkyl etherification of olefins with general alkyl groups. Primary, secondary and tertiary aliphatic acids are suitable for this reaction, delivering products with yields up to 97 %. Primary and secondary alcohols react well, affording products in up to 91 % yield.
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http://dx.doi.org/10.1002/anie.201612365 | DOI Listing |
Materials (Basel)
June 2024
Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, M. Strzody 9, 44-100 Gliwice, Poland.
This paper describes studies on the preparation of an o-cresol-furfural-formaldehyde resin in the presence of an alkaline catalyst and its modification with n-butanol or 2-ethylhexanol. The novelty of this research is to obtain a furfural-based resin of the resole type and its etherification. Such resins are not described in the literature and also are not available on the market.
View Article and Find Full Text PDFNat Prod Res
June 2024
Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, Kota Samarahan, Malaysia.
Org Biomol Chem
July 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.
Acid catalysed reductive etherification of -propargyl amino alcohols for the stereoselective synthesis of -2,5/2,6-disubstituted morpholines and -2,6/2,7-disubstituted oxazepanes has been developed. Mechanistic studies revealed that terminal alkynols gave morpholines a 6- hydroalkoxylation-isomerization-reduction cascade. Interestingly, an alkyne hydration-cyclization-reduction sequence is found to be involved in the formation of oxazepanes from alkyl substituted internal alkynols.
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August 2024
Department of chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039, India.
Demonstrated here is an external photo-sensitizer-free (auto-sensitized) singlet oxygen-enabled solvent-dependent tertiary hydroxylation and aryl-alkyl spiro-etherification of C3-maleimidated quinoxalines. Such "reagent-less" photo-oxygenation at Csp-H and etherification involving Csp-H/Csp-H are unparalleled. Possibly, the highly π-conjugated N-H tautomer allows the substrate to get excited by irradiation, and subsequently, it attains the triplet state via ISC.
View Article and Find Full Text PDFChem Rev
May 2024
Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods for their functionalization require them to first be converted into a more activated derivative, while recent years have seen a vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can be used toward this goal.
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